How to Raise a Seed Round in 2026: Ask Jason | E2294

Summary

Jason takes questions from the TWiST X group chat (400-500 members, with an inner 10-person “insiders” cohort). The core fundraising lesson: contact 150 firms, get 50 first meetings, convert 20 into second meetings, and close 2 term sheets. That’s the funnel. He compares it to content creation — most people stop after three videos, three pitches, three emails; the people who win do 150. Jason also pitches an idea for a “Founder Community College” / Venture University to compete with Kaufman Fellows ($80K tuition for two years), which he thinks he could deliver better with 10 students paying $50K each, funding two full-time staffers.

The rest covers: how to differentiate against frontier-lab products (community, marketplace, services around the LLM interface, with rental family/rental dad services as a fun example); what’s changed for early-stage evaluation (PMF achieved in days/weeks, no longer 6-12 months); why hardware is no longer a dirty word (“hardware is hard” → “hardware is sexy”); a pitch for Automatons-as-a-Service (AaaS) priced at $1-2/hour to undercut Amazon’s $27/hour package sorters; and a spicy named answer to “who in Silicon Valley do you not like?” — Sam Altman (for screwing Elon, his friend) and an unnamed military-tech founder. The episode ends with Lon’s recap of his 19-day Italy/Greece trip and a riff on the i360 selfie-stick guy ruining museums.

Highlights

The Real Seed-Round Funnel: 150 → 50 → 20 → 2

“Meetings to get two to give you a term sheet. That’s the funnel today. If you’re not doing that, you’re just not playing the game on the field.” — Jason Calacanis, 6:00

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PMF Used to Take 6-12 Months. Now It’s Weekends.

“And first customer is light product market fit. You can convince people to pay for anything, but let’s just say some level of product market fit. That’s down to weeks. It’s down to a weekend.” — Jason Calacanis, 21:00

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Why “Hardware is Hard” Became “Hardware is Sexy”

“Investors have totally 180’d their position on hardware. It used to be hardware is hard. I don’t want any part of it. Now it’s hardware is sexy.” — Jason Calacanis, 37:03

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Automatons-as-a-Service: $1-2 Per Hour

“If I was making Optimus or Figure, I would go to Amazon and say, what do you pay somebody to sort packages? They’d say it’s $27 an hour. And then fully baked, it’s $35 an hour. People sue us for workman’s comp…” — Jason Calacanis, 39:35

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Who in Silicon Valley Does Jason Not Like? Sam Altman.

“Sam Altman I don’t like because he screwed Elon and Elon’s my friend and I watched it happen but I I kind of liked Sam or I did like Sam interpersonally.” — Jason Calacanis, 44:17

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Museums Should Open at 6 AM and 8 PM with Premium Pricing

“100 euro, 100 dollar experience per person sounds insane. But by the way, if you’re an Uber driver or you’re a housekeeper in New York, you’re making 30, 40, 50 bucks an hour already. And that person might want to have an experience with 10% as many people there.” — Jason Calacanis, 53:37

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Key Points

• TWiST group chat funnel (1:43) - 400-500 in main chat, 10 in elite inner circle
• Match VC investing pattern to your stage (3:12) - “What they do is more important than what they tell you”
• 150 → 50 → 20 → 2 funnel (6:00) - The actual seed round math
• Memorable fund-instantly stories aren’t the norm (6:13) - They’re memorable BECAUSE they’re not
• Associate-in-training program (8:05) - Jason’s idea to charge $50K to train associates/founders
• Kaufman Fellows comparison (13:21) - $80K, 2 years, 1,000 fellows alumni
• Foundry University vs. Associate program (14:51) - Two tracks of company building
• $10M is the FU money threshold (16:22) - 5% return = $500K/yr after taxes = freedom
• Capital and time to PMF collapsed (18:01) - From $300K-$3M and 12 months to weeks/days
• Y Combinator → Antler → vibe coding evolution (20:43) - Each era halved capital required
• TWiST Bounties program (21:51) - Real-time fact-checker bounty got 15 submissions
• Differentiating from frontier labs (23:14) - LLM interfaces won’t add cluttered features; community, marketplace, services are moats
• Rental Family service / “Brendan Fraser movie” (26:57) - Japanese service inspiration for travel-planner-meets-marketplace
• The investor research grind (30:29) - Crunchbase, sales-funnel mindset, qualify each investor
• Whisper Network product (32:45) - Launch’s investor-introduction tool
• Investor pitches as sandwich-board signs in SF (35:03) - Creative outreach examples
• Hardware is sexy now (37:03) - VCs completely reversed
• Commoditized Chinese humanoid robots (39:00) - A few grand gets you a humanoid
• AaaS (Automatons-as-a-Service) (40:48) - $1-2/hour to undercut human workers
• Knightscope from TechCrunch 50 era (40:54) - Security robots, “won’t shoot as many people”
• Sam Altman: too self-interested (44:17) - Screwed Elon; New Yorker piece resonated
• Y Combinator + General Catalyst defending a founder (47:23) - Cane Corso allegation case
• Lon’s Italy trip recap (48:56) - Rome, Tuscany, Florence
• The selfie-stick / i360 guy gripe (51:14) - Documenting boring lives nobody will watch
• Museums should run 24 hours with premium pricing (53:14) - Uffizi-style time slots at $100/person
• Meta glasses exception (56:14) - The only camera-tech Jason approves at dinner

Mentions

Companies / Programs

• Quanto (2:30) - Richard Correll’s AI-powered wealth management for accounting firms
• True Ventures (30:29) - Friend invests only on referrals
• Y Combinator (20:43) - Reference investor; the cloud-era startup template
• Techstars (20:43) - Accelerator comparison
• Antler (20:43) - Accelerator comparison
• PearX (20:43) - Accelerator comparison
• Sequoia ARC (20:43) - Accelerator comparison
• Kaufman Fellows (12:48) - $80K, 2 years, ~1,000 alumni
• Launch Accelerator (31:13) - Jason’s program at launch.co/apply
• Foundry University (14:19) - Existing program Jason runs; considering partnership for a degree
• OpenAI (implicit) - The frontier lab to differentiate from
• Wealthfront (32:14) - Jason’s fintech track record
• Robinhood (32:14) - Jason’s fintech track record
• Uber (32:14) - Jason’s marketplace track record
• Thumbtack (32:14) - Jason’s marketplace track record
• Tesla / Optimus (39:35) - Humanoid robot reference
• Figure (39:35) - Humanoid robot reference
• Amazon (39:35) - $27/hr package sorters
• Knightscope (40:54) - Security robotics; TechCrunch 50 alum
• Eight Sleep, Whoop, Cafe X (per description) - Hardware examples
• General Catalyst (47:23) - Backed the Cane Corso case founder
• Groq (16:15) - Chamath’s reported 10-20% stake
• Ohalo (16:01) - Friedberg’s stock holding
• Grasshopper Bank (9:31) - Sponsor read
• LinkedIn Jobs (19:41) - Sponsor read
• Northwest Registered Agent (29:22) - Sponsor read

Products & Technologies

• Whisper Network (32:45) - Launch’s investor intro product
• Crunchbase (31:55) - Standard investor research tool
• Meta glasses (56:14) - Approved camera tech for museums
• Cane Corso (47:23) - Story Jason refused to react to on viral clip alone

People

• Richard Correll (2:30) - CEO of Quanto, first questioner
• Surge Dog (17:37) - X handle, asked about early-stage evaluation changes
• Mahima Galani (22:57) - Foundry University alum from Treya
• Sean Sully / @arugule (41:44) - Asked spicy “who don’t you like” question
• Yadon9884 (36:41) - Live stream viewer, hardware bootstrapping question
• Sam Altman (44:17) - Jason’s named answer
• Elon Musk (44:17) - Jason’s friend, allegedly screwed by Sam
• David Friedberg (16:01) - Not a billionaire (Jason’s claim)
• Chamath Palihapitiya (16:07) - Maybe not technically a billionaire (Jason’s claim)
• David Sacks (16:11) - Might be a billionaire
• Jenny Fielding (12:48) - Kaufman Fellow Jason knows
• Monique Woodard (12:48) - Kaufman Fellow Jason knows
• Brendan Fraser (27:00) - Star of Rental Family movie
• Mark Cuban (per podcast tradition) - Reference investor

Surprising Quotes

“Contact 150 firms, get 50 first meetings, convert 20 into second meetings, and close 2 term sheets.” — Jason Calacanis (paraphrased thesis), 6:00

“It’s a level of selfishness in decision making that and cutthroat…” — Jason Calacanis (on the unnamed military tech founder), 0:30

“I don’t think Friedberg’s a billionaire, maybe on paper with Ohalo stock.” — Jason Calacanis, 16:01

“Once you have $10 million, you have the FU money.” — Jason Calacanis, 16:22

“Sam Altman I don’t like because he screwed Elon and Elon’s my friend and I watched it happen.” — Jason Calacanis, 44:17

“What are we doing folks? What are we doing?” — Jason Calacanis (on the i360 selfie-stick guy), 57:04

Transcript

Jason Calacanis: 0:00 People in our secret group chat have questions for me. Some might be spicy.

Lon Harris: 0:02 What do you think founders should be doing to try to sort of give themselves a little bit of moat against OpenAI?

Jason Calacanis: 0:04 There’s always going to be a feature set that the interface of the large language model is not going to add.

Lon Harris: 0:09 Out of all the people in Silicon Valley, who’s the one person you really don’t like the most and why?

Jason Calacanis: 0:15 Some people have damaged the reputation of the industry and the user base. And then some people have just maybe screwed over friends of mine.

Jason Calacanis: 0:30 [bleep] I’ve been a consistent critic of. Every time he had a chance to do the right thing for humanity, he picked his own self-interest. It’s a level of selfishness in decision making that and cutthroat…

Jason Calacanis: 0:43 The two people I’m talking about are two of the most successful people ever in the history of business. All right.

Jason Calacanis: 0:51 Lon Harris is here, I’m Jason Calacanis. People in our secret group chat on X, formerly known as Twitter, have questions for me. I’m going to answer them.

Lon Harris: 1:31 Yeah. I would add if you’re very active in the group and participating and sharing great stuff, there is even a higher level insiders group.

Jason Calacanis: 1:43 It’s a funnel. We have everybody following the account, then we have 400 or 500 people in this crazy group chat, and then I think we have 10 people who are like the best people in the group chat.

Lon Harris: 2:18 Get out in the world, yeah.

Jason Calacanis: 2:23 Sure. That’s what I want to do. I need to get out in the world more. So yeah, more dinners, more hanging out, more live shows.

Lon Harris: 2:30 First question comes from Richard Correll of Quanto. It is an accounting firm in the age of AI.

Lon Harris: 3:00 Lon Harris wants to know your advice on how to combat the challenges facing startups with that early stage status, even when their tech is advanced and innovative.

Jason Calacanis: 3:12 Sure. Each investor has a different area of specialty and you should look at what stage of a startup they invest in most. And whatever they tell you is not as important as what they do, right?

Jason Calacanis: 6:00 Meetings to get two to give you a term sheet.

Lon Harris: 6:03 Wow.

Jason Calacanis: 6:04 That’s the funnel today.

Lon Harris: 6:05 Yeah.

Jason Calacanis: 6:06 If you’re not doing that, you’re just not playing the game on the field. You may hear of people who get funded…

Lon Harris: 6:12 Yeah.

Jason Calacanis: 6:13 You know, they take a meeting and they instantly get funded and they weren’t even looking for funding? Yeah, those are memorable stories because they are not the norm.

Lon Harris: 6:22 Right.

Jason Calacanis: 6:23 They’re notable because it’s not the norm. The norm that we see on the field is emailing and trying to get in touch with 150 different investors, getting on the phone with 50 of them.

Lon Harris: 7:01 Yeah. I think that’s… it’s interesting how many different sorts of fields and kinds of work that’s applicable to. Like people think to become a content creator, you just create like two or three videos.

Jason Calacanis: 8:05 So funny they mentioned this. I literally this weekend was asking about the accreditation laws and how I could give a degree. I was asking this because we have an associate in training program.

Jason Calacanis: 9:00 And they’re going to become all stars in our firm.

Jason Calacanis: 9:02 We want to replenish that. But I had so many people say to me, I would like to send my child to that. Can you charge me 60k a year for two years?

Lon Harris: 9:15 Right.

Jason Calacanis: 9:17 Continuing education. It turns out I’m not legally allowed to give a degree in being a founder or a degree in being a venture capitalist. I could give a certificate.

Lon Harris: 9:28 Right, but not a degree.

Jason Calacanis: 9:31 [Grasshopper Bank sponsor read]

Jason Calacanis: 10:32 And so that’s what I think a lot of people do with these continuing ed certificates. So I would have to partner with a local university in the US to do this.

Lon Harris: 10:45 Right.

Jason Calacanis: 10:47 Now, outside the US, there are some universities in the UK that will let you use their programs to do a UK accredited degree.

Lon Harris: 10:58 Okay.

Jason Calacanis: 11:00 And then there are islands, like there were some islands people would go get degrees in medical practices.

Lon Harris: 11:08 Sure, yeah. I mean, I know that’s a big Central American thing.

Jason Calacanis: 11:14 Right. And like dentistry and other things, and it does somehow work in the United States. They seem fugazi, fugazi.

Lon Harris: 11:26 shhh

Jason Calacanis: 11:28 But I have been thinking about this because I do think college is broken.

Jason Calacanis: 12:00 We could literally charge for it and literally say for $50,000, you can come work here for nine months out of the year, take your summers off or 10 months and for two years and then take on Kaufman Fellows.

Lon Harris: 12:47 Sure.

Jason Calacanis: 12:48 But they’ve had a thousand fellows, some of those you might know. There’s Jenny Fielding. I know her. There’s Monique Woodard. I’m an LP.

Lon Harris: 13:21 Yeah, no, Jacob looked it up. Producer Jacob looked it up for us. The Kaufman Fellows two-year program tuition is $80,000.

Jason Calacanis: 13:31 So I think I could have 10 people in this program, charge them 50k each, that’d be 500k. Then I could hire two full-time people to work on it.

Lon Harris: 13:59 Yeah, Zoom meetings probably mostly, but…

Jason Calacanis: 14:02 I wonder like what the actual curriculum is. If somebody could send me the curriculum or send me like the agenda.

Lon Harris: 14:18 Yeah.

Jason Calacanis: 14:19 I am thinking on a competitive basis, like maybe I could create a better program. And then for Foundry University, I would be fine with partnering with a university.

Lon Harris: 14:37 There’s probably some young people that would be interested in entrepreneurship, but wouldn’t even know where to get started.

Jason Calacanis: 14:51 Or maybe you put the two together and it’s just company building and you have two tracks, the Foundry University track and the associate track.

Lon Harris: 14:59 Right.

Jason Calacanis: 15:00 To the Venture University track, you have the two tracks and you major in one, minor in the other, but you learn both sides of the table.

Lon Harris: 15:08 And I mean we also I bet you Kaufman Fellows is not doing media training.

Jason Calacanis: 15:41 Yeah, for sure. Now unfortunately because some idiot started a podcast about startups 16 years ago, now every venture capitalist has to have a podcast.

Lon Harris: 15:53 Especially since one of them’s not a billionaire.

Jason Calacanis: 15:57 I actually think three of them are not billionaires technically.

Lon Harris: 15:59 Really? Wow, that’s breaking news.

Jason Calacanis: 16:01 Huge if true. Yeah, I don’t think Friedberg’s a billionaire, maybe on paper with Ohalo stock.

Lon Harris: 16:07 I don’t think Chamath’s a billionaire? I don’t know, people just refer to you all as billionaires.

Jason Calacanis: 16:11 Sax might be a billionaire, I don’t know. Sax and Chamath maybe pretty close.

Lon Harris: 16:15 Maybe. Chamath after that Groq deal, come on!

Jason Calacanis: 16:18 I think he probably owned 10, 20 percent of that.

Lon Harris: 16:20 Yeah, and maybe probably not liquid.

Jason Calacanis: 16:22 Yeah, the always the thing. And then who cares, like honestly. The more I look at wealth and wealth creation, once you get past like this basic $10 million mark, you have the FU money.

Lon Harris: 16:46 And it’s exactly $10 million. That’s exactly the FUM number. FUM starts at 10 million.

Jason Calacanis: 16:54 You make 5% on your money, which is a half million dollars a year, which means after taxes, 400, 500 thousand a year, you can just exist.

Lon Harris: 17:08 Yeah, you’d be back in Florence right now.

Jason Calacanis: 17:11 You’d be back in Florence. How was your trip by the way?

Lon Harris: 17:15 Amazing trip, I had a great time. Rome, Rome and Tuscany.

Jason Calacanis: 17:17 How many days did I give you off? Jesus.

Lon Harris: 17:23 It was, you kept saying 22. It was technically 19 days, and a lot of those were weekends. So it was like 14 work days off total.

Jason Calacanis: 17:26 It felt like you were gone for two months. My god. You definitely have job security.

Lon Harris: 17:37 All right, let’s go into number three. This is from Surge Dog, also on X. If you compare early-stage startups today to 10 years ago, what has changed the most in how you evaluate them?

Lon Harris: 18:00 For you as an investor in early stage.

Jason Calacanis: 18:01 Yeah, I mean, the number one thing is the amount of capital it takes to get a product to market and the amount of time it takes to get product market fit. That is dramatically decreased.

Jason Calacanis: 19:41 [LinkedIn Jobs sponsor read]

Jason Calacanis: 20:43 Then the Y Combinator era, the cloud computing era meant you work at home, three people, you eat ramen for 300k, you could stand up a startup in under six months. Now it went to like 30k.

Jason Calacanis: 21:00 You and your partners never met in person and you just shipped and you vibe coded stuff and you got your first customer then you applied to Y Combinator or Techstars or Antler.

Lon Harris: 21:27 Yeah.

Jason Calacanis: 21:27 And first customer is light product market fit. You can convince people to pay for anything, but let’s just say some level of product market fit. That’s down to weeks. It’s down to a weekend.

Lon Harris: 21:43 Yeah, I was going to say it’s down to days. We’ve seen companies on the last few months on the show that are literally like, oh, I built this 14 days ago.

Jason Calacanis: 21:51 Our bounties program is a perfect example of that. We have two bounties out this week in startups.com/bounties.

Lon Harris: 22:45 And by the time this airs on VOD, we’ll have already picked a winner for our sidecast live producer bounty.

Jason Calacanis: 22:51 Or winners. Or multiple winners. You never know.

Lon Harris: 22:57 All right. Next question from Foundry University vet Mahima Galani of a company called Treya. She wants to know how should startups think about differentiating when frontier labs release products in their space?

Jason Calacanis: 23:14 Absolutely. So there’s always going to be a feature set that the interface of the large language model is not going to add because of clutter and confusion. So let’s take travel.

Lon Harris: 24:00 That was great.

Jason Calacanis: 24:00 Rome was like one of the best previews I’ve ever seen. It’s in our database, it’s not public because it’s shut down.

Jason Calacanis: 24:02 Yeah, it was great. ‘What should I do over my 19 days because my boss is so goddamn accommodating?’

Lon Harris: 24:30 Mmm-hmm.

Jason Calacanis: 24:31 The community, the support, these extra features, they’re not what ChatGPT’s gonna work on. They’re just gonna give you your basic output.

Lon Harris: 25:36 I was just going to say, having just planned a trip, you do look things up on AI, it’s natural. I use it in place of a search engine.

Jason Calacanis: 25:58 I think the community, multiplayer mode, support services around those things, they’re just not going to do that. They’re not going to create a marketplace with local guides.

Lon Harris: 26:57 Fascinating.

Jason Calacanis: 26:58 Yeah, there was a movie about him.

Jason Calacanis: 27:00 Brendan Fraser was in about like—

Lon Harris: 27:02 Rental family, rental family, yes.

Jason Calacanis: 27:04 And the concept is?

Lon Harris: 27:05 He’s an American actor and he’s hired to pretend to be like a surrogate father in this family that doesn’t have a dad around.

Jason Calacanis: 27:15 Yeah, it’s a real service.

Lon Harris: 27:22 The you can like rent a fake family member for occasions or for times where you are particularly missing having like a dad around.

Jason Calacanis: 27:28 And then he becomes of course bonded with the family and it becomes a sweet story.

Jason Calacanis: 27:33 You could also do rent an old guy for fun.

Lon Harris: 27:37 Yes. So that is a thing.

Jason Calacanis: 27:39 You rent an old guy.

Lon Harris: 27:41 And there’s rent-a-boyfriend, rent-a-girlfriend services, those get talked about a lot and it’s not a sex worker thing.

Jason Calacanis: 27:53 Yeah.

Lon Harris: 27:54 But the renting a food thing is like that’s even better so let’s say you have this idea for an AI planner.

Jason Calacanis: 28:03 Okay.

Lon Harris: 28:05 So you get the basic chat gpt features for free but then we can also connect you with somebody who books this or gets in line for you, brings you, translates, it sits with you.

Jason Calacanis: 28:18 Sure. Yeah, in Rome we booked a uh—

Lon Harris: 28:21 One of those golf cart tours where the guys drive you around in the golf cart and we got to go into a bunch of crypts and stuff under the churches.

Jason Calacanis: 28:34 Genius.

Lon Harris: 28:35 So yeah, I think that’s yeah, there’s a service there if you can find your sort of spot in the stack.

Jason Calacanis: 28:46 So from triperidot on X, they’re a dating app for serious daters. They compare it to being like being set up by a friend.

Lon Harris: 28:54 By women, for women, a new take on the dating app, that is their business. Their question, and I quote: ‘Founders are often told to find the right investor but most advice reduces to stage sector or warm intros.’

Jason Calacanis: 29:22 [Northwest Registered Agent sponsor read]

Jason Calacanis: 30:29 Okay, so there are investors who have all different sets of signal and processes in which they invest. I have a friend who’s an investor at True Ventures. He only invests on things that come from referrals.

Jason Calacanis: 31:13 Then there are people like Y Combinator or us, you come to launch.co/apply, we meet with 10% of the companies that apply every week. So some weeks we get 200 people applying, sometimes 500.

Lon Harris: 31:25 Yeah, it’s a lot.

Lon Harris: 31:28 Yeah.

Jason Calacanis: 31:29 So we meet with those 25. At the end of the year, all said and done, we’ve done 3, 4, 5,000 meetings and we’ve invested in 100 companies, culled down from 10 to 20,000 applications.

Jason Calacanis: 31:43 But we don’t invest in biotech or military tech right now. We actually started with military tech, but we didn’t do biotech.

Jason Calacanis: 31:55 So figuring that out is hard and it’s work. The best thing to do is to study what people have already done. You get a Crunchbase account.

Jason Calacanis: 32:14 So if you’re a marketplace and they did Uber or Thumbtack, like I did. Or they’re doing fintech like I did Wealthfront and Robinhood, you can know that when you come to me, we share that.

Jason Calacanis: 32:45 So that’s your job, and you have realized now as an investor that this is not a clean, easy-to-navigate marketplace. It’s a bit bespoke and underground. We have a product called Whisper Network.

Jason Calacanis: 33:00 And search through and put in their materials, ask us for an introduction, and even with that tool, it’s still hard. You’re hunting, you’re packing, you’re doing research.

Lon Harris: 33:30 Yeah.

Jason Calacanis: 33:31 And that’s what you need to do. You have to look at fundraising as a full-time job.

Lon Harris: 33:41 Sort of the same answers as number one, like it’s just it’s about legwork and putting in the hours.

Jason Calacanis: 33:52 It’s a sales funnel. You have to qualify each sale. Are you qualifying each investor? Do they invest — have they invested in your stage?

Lon Harris: 34:46 Yeah, and you have to treat it as such.

Jason Calacanis: 35:03 And you know, you can be creative about it. Like there was somebody I saw who went to San Francisco and put the pitch for their startup [as a sandwich-board sign].

Jason Calacanis: 36:00 On your podcast because I emailed them and told them it was on podcast. That helping people without expectations of return is a unique part of the tech industry.

Lon Harris: 36:12 We found this post a guy who put a sign on his laptop. Yeah, a guy put a sign on his laptop ‘AI B2B startup’.

Jason Calacanis: 36:32 Love it.

Lon Harris: 36:33 There you go. Yeah. People see you coding. All right, we got a what do you want to do one or two more?

Jason Calacanis: 36:40 Sure. Keep going. My energy’s good.

Lon Harris: 36:41 Good question in from one of the live viewers right here on this very live stream from @yadon9884. What’s the best path for a bootstrap hardware founder once the prototype is ready?

Jason Calacanis: 37:03 Yeah, I think you should get investors if you’re at that point. And investors have totally 180’d their position on hardware. It used to be hardware is hard. I don’t want any part of it. Now it’s hardware is sexy.

Lon Harris: 39:00 Yeah, and that’s going to really supercharge this whole thing. Like you’re already you could drop a few grand and get a Chinese humanoid robot at this point.

Jason Calacanis: 39:12 I think figuring out what to do with commoditized robots is going to be a very interesting business. And I think they ultimately will be a dollar or two dollars an hour is my guess.

Lon Harris: 39:26 Oh, you think it’s going to be like robots as a service?

Jason Calacanis: 39:35 If I was making Optimus or Figure, I would go to Amazon and say, what do you pay somebody to sort packages? They’d say it’s $27 an hour. And then fully baked, it’s $35 an hour.

Lon Harris: 40:44 Great acronym too. ASS, Automatons as a Service. It’s going to be great.

Jason Calacanis: 40:48 Automatons as a service. ASS, yes. AAS would be your acronym, yeah.

Lon Harris: 40:52 They’ll cover your ass, yeah.

Jason Calacanis: 40:54 There you go. I think they’re going to be great. We had a security one, Knightscope, that had been at like TechCrunch 50 or one of the early launch festivals.

Lon Harris: 41:26 It’s not going to accidentally shoot as many people probably, hopefully, as the human security guard.

Jason Calacanis: 41:30 But good luck with your hardware startup. It’s a good time now.

Lon Harris: 41:33 All right. We got a question from Jacob. We got a very spicy question that you’re free to punt.

Jason Calacanis: 41:43 Give me the spicy and then we’ll do the video.

Lon Harris: 41:44 All right. From Sean Sully, aka @arugule on X, out of all the people in Silicon Valley, who’s the one person you really don’t like the most and why?

Jason Calacanis: 41:54 Who don’t I like?

Lon Harris: 41:56 Yeah, the one person you don’t like. I think you could pick your reason.

Lon Harris: 42:00 Things, it’s a personality conflict whichever, you take your pick. I have some guesses but I’d like to hear your opinion.

Jason Calacanis: 42:08 Well, listen, I would say you know we all operate in the same ecosystem of users and some people I think have damaged the reputation of the industry and the user base. And then some people have just maybe screwed over friends of mine.

Lon Harris: 44:16 Well I mean we’ve seen…

Jason Calacanis: 44:17 Sam Altman I don’t like because he screwed Elon and Elon’s my friend and I watched it happen but I kind of liked Sam or I did like Sam interpersonally we always had some like interesting things.

Lon Harris: 44:50 Yeah they’re doing alright.

Lon Harris: 44:51 So in some ways being able to make self-interested decisions and not worry about what people think about you and not worry about losing and burning relationships…

Jason Calacanis: 44:57 For sure.

Lon Harris: 44:58 Is…

Jason Calacanis: 45:00 Is a quick path to extraordinary success.

Lon Harris: 45:02 Yes, I think being a like high-level tech CEO definitely self-selects for some of those qualities.

Jason Calacanis: 45:14 I mean, the number of people who called in that piece in the New Yorker, which, you know, these press pieces it’s probably 60% true, 40% true, 80% true, who knows?

Lon Harris: 45:59 I mean, when you’re writing a piece like that…

Jason Calacanis: 46:01 So anyway, that’s the answer. There you go.

Lon Harris: 46:03 Fair enough.

Jason Calacanis: 46:05 And it’s not personal, so, everybody wants to make it personal, like, I’ll bring up maybe the guy with the wrong, the guy in military tech.

Lon Harris: 47:18 When you podcast every day, you’re just reacting, you’re doing hot takes, it can you get caught up in the moment.

Jason Calacanis: 47:23 Well but you see how I do it, we were doing a recording before this and people were asking me about a case and, Y Combinator and General Catalyst supporting a founder who allegedly did [Cane Corso situation].

Jason Calacanis: 48:00 Most people just run with a Cane Corso, the great story, or like some viral clip, and I’m like, just so you know, that viral clip could be AI, it could be an old clip.

Lon Harris: 48:28 I think that’s a good lesson for even if you’re not hosting a podcast, even just in your everyday life. In 2026, you’ve got to take that beat.

Jason Calacanis: 48:56 Lon, this was your first trip to Italy?

Lon Harris: 48:58 This was my first time ever in Italy, yes.

Jason Calacanis: 49:01 That’s true. Okay. So, and you went to Greece?

Lon Harris: 49:03 Oh, you went to Greece as well? Okay. I went to Santorini and Mykonos.

Jason Calacanis: 49:09 Amazing.

Lon Harris: 49:10 It was amazing.

Jason Calacanis: 49:10 So give me your general impression of Greece and Italy.

Lon Harris: 49:19 Yeah, so I went, I did a week in Rome. We stayed in an Airbnb right by the Castel Sant’Angelo, right sort of the middle of the city. Staying in the Airbnb.

Jason Calacanis: 50:08 I think I went to both of those. That’s great.

Lon Harris: 50:10 Yeah, yeah. They’re one of the places they take a huge wheel of cheese and they pour brandy in it and then they light it on fire.

Lon Harris: 51:00 You can get the Birth of Venus on like a mousepad. Like, you don’t need your own photo.

Jason Calacanis: 51:06 I think this is a gripe that’s worth noting.

Lon Harris: 51:10 Yeah.

Jason Calacanis: 51:10 Just be in the moment, folks, just be in the moment.

Lon Harris: 51:14 And this I’ll tell you the thing that makes me crazy in these places: The selfie stick.

Jason Calacanis: 51:17 That, yes.

Lon Harris: 51:18 Or the i360 guy. You know the i360 guy?

Jason Calacanis: 51:22 Of course.

Lon Harris: 51:24 With the stick, and it goes up, and he’s got to walk around, and he’s got to have a 360 view…

Jason Calacanis: 51:30 That he’s never going to look at. But the 360 guy is worse than the selfie guy.

Lon Harris: 51:34 Yeah.

Jason Calacanis: 51:35 The selfie guy’s got his iPhone on the stick, whatever. These guys are walking through Vegas casinos and I’m like, what are you documenting? Your life is incredibly boring.

Lon Harris: 51:54 Nobody cares.

Jason Calacanis: 51:55 You’re never looking at these things. If you want to take a quick photo of yourself in front of your favorite piece, totally fine.

Lon Harris: 52:08 Right, and I did. I posted a few of them to Twitter.

Jason Calacanis: 52:21 Just take it in!

Lon Harris: 52:23 And like we went to a Rothko exhibit as well in Florence, like a modern museum, and it’s like those paintings, it’s being in the room with it, that’s the point.

Jason Calacanis: 52:34 So here’s my idea for these museums: 24 hours. And increase the price to go a little bit.

Lon Harris: 52:42 Mm.

Jason Calacanis: 52:42 So, or maybe like on the off hours, you pay a premium.

Lon Harris: 52:45 Oh, sure.

Jason Calacanis: 52:46 I would like — because these all close at 6 o’clock, right? They’re done.

Lon Harris: 52:50 Yeah, it’s like Uffizi I think is yeah, it’s like 10 AM to like 4:30, but you have to get a time.

Jason Calacanis: 52:57 And there’s like a VIP line, you pay an extra couple of euros. So what did you pay, 10 euros or something? It’s not expensive.

Lon Harris: 53:02 No, it was I think it was like 30 euros a piece.

Jason Calacanis: 53:13 Here’s my idea.

Lon Harris: 53:14 Yeah.

Jason Calacanis: 53:15 The place closes — the last entrance is 4:30, which means they’re kicking you out at 6:00. 6:00 to 8:00, 8:00 to 10:00, 10:00 to 12:00, 12:00 to 2:00, 6:00 AM to 8:00 AM.

Lon Harris: 53:37 Yeah.

Jason Calacanis: 53:37 Now, 100 euro, 100 dollar experience per person sounds insane. But by the way, if you’re an Uber driver or you’re a housekeeper in New York, you’re making 30, 40, 50 bucks an hour already.

Lon Harris: 53:52 Yeah.

Jason Calacanis: 53:53 And that person might want to have an experience with 10% as many people there or 20% as many people there.

Lon Harris: 53:58 Yeah, it would be a totally different experience to go with a small group.

Lon Harris: 54:00 Really like soak it in on your own and have the time instead of being pushed around.

Jason Calacanis: 54:07 I would have loved to go to dinner and then I like to do my after-dinner walk, because I’m old and, you know, controlling my weight. I would love to do my two-hour walk in the Louvre.

Lon Harris: 54:36 Yeah, because also I had the same experience in the British Museum too in London.

Jason Calacanis: 54:47 Did you go to the Florence gelato place that I told you about?

Lon Harris: 54:51 You know, I did. I went to a gelato place in Florence but we were only there for 24 hours.

Jason Calacanis: 55:25 Santorini, beautiful, right? On that hillside. Did you get to go on the donkey ride up and down Santorini?

Lon Harris: 55:31 No, I felt bad for the donkey. I don’t want to subject a donkey to my 200 pounds.

Jason Calacanis: 55:43 Well, this is why ro.co/twist will get you down to 180 and you’ll be fighting weight.

Lon Harris: 55:54 Yes, it leads up to Oia. Oia, the sort of that it’s the city when you think of Santorini and you see the Instagram posts with the white houses and the blue domed churches, that’s Oia.

Jason Calacanis: 56:14 I’m glad you got to take some time off. Me too. And this is where I don’t have a problem with the Meta glasses actually.

Lon Harris: 56:35 I don’t think you’re really going to get a lot out of that after the fact.

Jason Calacanis: 56:49 Take 10 pictures. Okay? Take 10 pictures. You yourself with the front, yourself in front of your favorite piece of art that you saw.

Lon Harris: 57:00 I took a ton, but when you’re standing in front of a Rothko, you don’t need to have your camera.

Jason Calacanis: 57:04 What are we doing folks?

Jason Calacanis: 57:09 What are we doing?

Lon Harris: 57:11 Yeah.

Jason Calacanis: 57:12 All right everybody, it’s been another great. Twist is in the can. Bye-bye.

Lon Harris: 57:16 Bye-bye.